tert-butyl N-(4-aminobutyl)carbamate → HCID 58945263, compound

HRID 659995Notes

Reaction equation

HRID 659995 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]>CC(O)C.Cl.[NH4+].[Cl-].CS(C)=O>[C:17]([O:16][C:15](=[O:21])[NH:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 709434,6-Dichloropyrimidine

Product 1

HCID 58945263HCID 58945263, compoundYield 41%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

4,6-Dichloropyrimidine (4.14 mmol) and tert-butyl 4-aminobutylcarbamate (4.14 mmol) were dissolved in 13 ml of 2-propanol, and 3 drops of 3M aq. HCl were added. The mixture was heated in a Personal Chemistry Optimizer microwave system at 100° C. for 900 s. The reaction mixture was diluted with sat. aq. NH4Cl-solution (50 ml) and extracted with EtOAc (2×). Drying of the organic layer (Na2SO4) and evaporation of the solvent under reduced pressure yielded the crude product, which was taken up in DMSO (2.5 ml) and purified via prep.-HPLC (XTerra Prep. MS C18 5 μm, 19×150 mm, gradient from water to MeCN over 14 min), yielding 41% of a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialDrying of the organic layer (Na2SO4) and evaporation of the solvent under reduced pressure
  3. customyielded the crude product, which
  4. custompurified via prep.-HPLC (XTerra Prep

Sources & evidence

ORD record
ord-edd0176435804b50b5d1681e3af363bb
Source dataset
uspto-grants-2011_12
Patent number
US08084457B2

Reaction notes

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